Tert-butyl 2-(4-morpholinoanilino)-4-phenethylbenzoate → 2-(4-Morpholinoanilino)-4-phenethylbenzoic acid

HRID 2191752Notes

Reaction equation

HRID 2191752 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:34]=[CH:33][C:10]([NH:11][C:12]3[CH:24]=[C:23]([CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:22]=[CH:21][C:13]=3[C:14]([O:16]C(C)(C)C)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([NH:11][C:12]3[CH:24]=[C:23]([CH2:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:22]=[CH:21][C:13]=3[C:14]([OH:16])=[O:15])=[CH:33][CH:34]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 68957258Tert-butyl 2-(4-morpholinoanilino)-4-phenethylbenzoate

Product 1

HCID 576680262-(4-Morpholinoanilino)-4-phenethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid 10 mL was added to the obtained tert-butyl 2-(4-morpholinoanilino)-4-phenethylbenzoate, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 45-80% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 2-(4-morpholinoanilino)-4-phenethylbenzoic acid 11 mg of a white solid.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ead2d1257475487a8681386076f82077
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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